arecoline   Click here for help

GtoPdb Ligand ID: 296

Synonyms: methylarecaiden | methylarecaidin | taeniolin
Comment: Arecoline is an alkaloid derived from the betel nut. It acts as a cholinomimetic.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 2
Topological polar surface area 29.54
Molecular weight 155.09
XLogP 0.17
No. Lipinski's rules broken 0
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Canonical SMILES COC(=O)C1=CCCN(C1)C
InChI InChI=1S/C8H13NO2/c1-9-5-3-4-7(6-9)8(10)11-2/h4H,3,5-6H2,1-2H3
1. Christie JE, Shering A, Ferguson J, Glen AI. (1981)
Physostigmine and arecoline: effects of intravenous infusions in Alzheimer presenile dementia.
Br J Psychiatry, 138: 46-50. [PMID:7023592]
2. Ghelardini C, Galeotti N, Lelli C, Bartolini A. (2001)
M1 receptor activation is a requirement for arecoline analgesia.
Farmaco, 56 (5-7): 383-5. [PMID:11482763]
3. Jakubík J, Bacáková L, El-Fakahany EE, Tucek S. (1997)
Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors.
Mol Pharmacol, 52 (1): 172-9. [PMID:9224827]
4. Mei L, Lai J, Roeske WR, Fraser CM, Venter JC, Yamamura HI. (1989)
Pharmacological characterization of the M1 muscarinic receptors expressed in murine fibroblast B82 cells.
J Pharmacol Exp Ther, 248 (2): 661-70. [PMID:2537406]
5. Ozenil M, Pacher K, Balber T, Vraka C, Roller A, Holzer W, Spreitzer H, Mitterhauser M, Wadsak W, Hacker M et al.. (2020)
Enhanced arecoline derivatives as muscarinic acetylcholine receptor M1 ligands for potential application as PET radiotracers.
Eur J Med Chem, 204: 112623. [PMID:32717485]
6. Richards MH, van Giersbergen PL. (1995)
Human muscarinic receptors expressed in A9L and CHO cells: activation by full and partial agonists.
Br J Pharmacol, 114 (6): 1241-9. [PMID:7620715]
7. Xie DP, Chen LB, Liu CY, Zhang CL, Liu KJ, Wang PS. (2004)
Arecoline excites the colonic smooth muscle motility via M3 receptor in rabbits.
Chin J Physiol, 47 (2): 89-94. [PMID:15481791]
8. Yang YR, Chang KC, Chen CL, Chiu TH. (2000)
Arecoline excites rat locus coeruleus neurons by activating the M2-muscarinic receptor.
Chin J Physiol, 43 (1): 23-8. [PMID:10857465]